Amidrazones and their use as insecticidal and acaricidal agents

ABSTRACT

There are provided substituted acid amide, arylhydrazone compounds (amaidrazones) of formula I ##STR1## the use thereof for the control of insect and acarid pests and methods and compositions for the protection of crops from the damage and loss caused by said pests.

This is a divisional of application Ser. No. 07/998,105 filed on Dec. 29, 1992, now U.S. Pat. No. 5,420,165.

BACKGROUND OF THE INVENTION

Certain insect and acarid pests are harmful and cause enormous losses annually in agricultural crops, stored products and human and animal health. It is an object of this invention to provide substituted acid amide, N-arylhydrazone compounds (amaidrazones) which are effective agents for the control of pestiferous insects and acarina.

It is another object of this invention to provide a method for the protection of important agronomic crops from-the harmful and damaging effects caused by insect and acarid pests.

It is a further object of this invention to provide insecticidal and acaricidal compositions.

SUMMARY OF THE INVENTION

The present invention provides a method for the control of insects or acarina which comprises contacting said insects or acarina or their food supply, breeding ground or habitat with an insecticidally effective amount of an amidrazone compound of formula I ##STR2## wherein A is C--R₄ or N;

B is C--R₅ or N;

W is C--R₆ or N with the proviso that one of A, B or W must be other than N;

Y is hydrogen, halogen, CN, NO₂, C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, C₁ -C₆ alkoxy or C₁ -C₆ halo-alkoxy;

n is an integer of 0, 1 or 2;

R is hydrogen, C₁ -C₁₀ alkyl optionally substituted with one or more halogens, C₃ -C₆ cycloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, (C₁ -C₄ alkyl)SO_(x), (C₁ -C₄ haloalkyl)SO_(x), phenyl optionally substituted with one to three halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, (C₁ -C₄ alkyl)SO_(x), (C₁ -C₄ haloalkyl)SO_(x), NO₂ or CN groups, or phenoxy optionally substituted with one to three halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ -haloalkoxy, (C₁ -C₄ alkyl)SO_(x), (C₁ -C₄ -haloalkayl) SO_(x), NO₂ or CN groups,

C₃ -C₁₂ cycloalakyl optionally substituted with one or more halogens, C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ -haloalkoxy, (C₁ -C₄ alkyl)SO_(x), (C₁ -C₄ haloalkyl)SO_(x), phenyl optionally substituted with one to three halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, NO₂ or CN groups, or phenoxy optionally substituted with one to three halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalky, C₁ -C₄ alkoxy, C₁ -C₄ -haloalkoxy, NO₂ or CN groups, or

phenyl optionally substituted with one or more halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, NO₂ or CN groups;

R₁ is hydrogen or C₁ -C₄ alkyl;

R₂ and R₃ are each independently hydrogen,

C₁ -C₁₀ alkyl optionally substituted with one or more halogen, hydroxy, C₁ -C₄ alkoxy, (C₁ -C₄ alkyl)SO_(x), CONR₇ R₈, CO₂ R₉, R₁₀, R₁₁, C₃ -C₆ cycloalkyl optionally substituted with one to three halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ haloalkoxy, NO₂ or CN groups, phenyl optionally substituted with one or more halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkayl, C₁ -C₄ alkoxy, C₁ -C₄ -haloalkoxy, CO₂ or CN groups, or pyridyl optionally substituted with one or more halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ -haloalkoxy, NO₂ or CN groups,

C₃ -C₁₀ alkenyl optionally substituted with one or more halogen, hydroxy, C₁ -C₄ -alkoxy, (C₁ -C₄ alkyl)SO_(x), CONR₇ R₈, CO₂ R₉, R₁₀, R₁₁, C₃ -C₆ cycloalkyl optionally substituted with one to three halogen, C₁ -C₄ alkyl, C₁ -C₄ halo-alkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalakoxy, NO₂ or CN groups, phenyl optionally substituted with one or more halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ -haloalkoxy, CO₂ or CN groups, or pyridyl optionally substituted with one or more halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ -haloalkoxy, NO₂ or CN groups,

C₃ -C₁₀ alkynyl optionally substituted with one or more halogen, hydroxy, C₁ -C₄ -alkoxy, (C₁ -C₄ alkyl)SO_(x), CONR₇ R₈, CO₂ R₉, R₁₀, R₁₁, C₃ -C₆ cycloalkyl optionally substituted with one to three halogen, C₁ -C₄ alkyl, C₁ -C₄ halo-alkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, NO₂ or CN groups, phenyl optionally substituted with one or more halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ -haloalkoxy, CO₂ or CN groups, or pyridyl optionally substituted with one or more halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ -haloalkoxy, NO₂ or CN groups,

C₃ -C₁₂ cycloalkyl optionally substituted with one or more halogen, hydroxy, C₁ -C₄ -alkoxy, (C₁ -C₄ alkyl)SO_(x), CONR₇ R₈, CO₂ R₉, R₁₀, R₁₁, C₃ -C₆ cycloalkyl optionally substituted with one to three halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ -haloalkoxy, NO₂ or CN groups, phenyl optionally substituted with one or more halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ -haloakoxy, CO₂ or CN groups, or pyridyl optionally substituted with one or more halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ -haloalkoxy, NO₂ or CN groups or

R₂ and R₃ may be taken together to form a ring represented by the structure ##STR3## R₄, R₅ and R₆ are each independently hydrogen, halogen, CN, NO₂, (C₁ -C₄ alkyl )SO_(x), (C₁ -C₄ -haloalkyl) SO_(x), C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, C₁ -C₆ alkoxy or C₁ -C₆ haloalkoxy,

R₇, R₈ and R₉ are each independently hydrogen or C₁ -C₄ alkyl;

R₁₀ is NR₁₂ R₁₃, ##STR4## R₁₁ is ##STR5## R₁₂, R₁₃, R₁₄ and R₁₅ are each independently hydrogen or C₁ -C₄ alkyl;

X is O, S or NR₁₄ ;

r is an integer of 0 or 1;

p and m are each independently an integer of 0, 1, 2 or 3 with the provisos that only one of p, m or r can be 0 and that the sum of p+m+r must be 4, 5 or 6;

x is an integer of 0, 1 or 2; or the acid addition salts thereof.

The present invention further provides N-arylamidrazone compounds of formula I wherein A, B, W, Y, n, R, R₁, R₂, and R₃ are as described hereinabove with the proviso that when all of A, B and W are other than N, then R and one of R₂ or R₃ must be other than hydrogen and with the further proviso that when one of A, B or W is N, then Y, R₄, R₅ or R₆ must be other than C₁ -C₁₀ alkyl.

Compositions and methods for the protection of growing plants from attack and infestation by insects and acarina are also provided.

DETAILED DESCRIPTION OF THE INVENTION

A variety of insects and acarina cause great economic loss by damaging or destroying agricultural crops and other valuable plants; by aiding in the spread and development of bacteria, fungi and viruses that produce diseases of plants; and by destroying or lowering the value of stored foods, other products and possessions. Insects and acarina present some of the farmers' greatest problems the world over. The need for alternative and effective insect and acarid control is a global concern.

It has now been found that the substituted acid amide, N-arylhydrazone compounds of formula I are especially efficacious insecticidal and acaricidal agents, particularly against Coleoptera, Lepidoptera and Acarina.

The formula I amidrazone compounds of the present invention have the structural formula ##STR6## wherein A, B, W, Y, n, R, R₁, R₂ and R₃ are described hereinabove. The term halogen as used in the specification and claims designates chlorine, fluorine, bromine or iodine. The term acid addition salts designates those salts formed by acids commonly known in the art such as hydrogen chloride, hydrogen bromide, hydrogen bisulfate, hemi-hydrogen sulfate and the like. In the above definition when n is O then Y is hydrogen.

Preferred compounds of the invention are those wherein R, R₂ and R₃ are each independently hydrogen or C₁ -C₆ alkyl, A is C--R₄, B is C--R₅, W is C--R₆, Y is halogen and n is 1. Particularly preferred compounds are those wherein R₁ is hydrogen, R₄ is halogen, R₅ is hydrogen and/or R₆ is C₁ -C₆ alkyl substituted with one or more halogens, preferably trifluoromethyl.

Other preferred compounds of the invention are compounds having the structure ##STR7## wherein R is C₁ -C₁₀ alkyl;

R₁ is hydrogen or C₁ -C₄ alkyl;

R₂ is C₁ -C₁₀ alkyl;

R₃ is hydrogen or C₁ -C₁₀ alkyl; and

R₄, R₆ and Y are each independently hydrogen, halogen, CN, NO₂, C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, C₁ -C₆ alkoxy, or C₁ -C₆ haloalkoxy.

The N-arylamidrazones of formula I may be prepared by reacting an acid chlorides hydrazone (hydrazinoyl chloride) of formula II with an amine compound, HNR₂ R₃, as shown in flow diagram I, ##STR8##

Compounds of formula II may be prepared by reacting a suitable arylhydrazine of formula III with the appropriate acid chloride, RCOC1, to obtain an N-arylhydrazide of formula IV and reacting the formula IV hydrazide with a chlorinating agent such as thionyl chloride to give the desired formula II N-arylhdrozinoyl chloride product. The reaction is illustrated in flow diagram II. ##STR9##

The substituted N-arylamidrazone compounds of the present invention are effective for controlling insect and acarid pests. Said compounds are also effective for protecting growing or harvested crops from attack and infestation by such pests.

In practice, generally about 10 ppm to 10,000 ppm, preferably about 100 to 5,000 ppm of the formula I compound dispersed in a liquid carrier, when applied to the plants or the soil or water in which they are growing, is effective to protect the plants from insect and acarina attack and infestation. Soil application of the formula I compounds is particularly effective for the control of the post-embryonic development stages of Coleoptera and Diptera. Applications, such as spray applications, of compositions of the invention are generally effective at rates which provide about 0.125 kg/ha to about 250 kg/ha, preferably about 10 kg/ha to 100 kg/ha. Of course, it is contemplated that higher or lower rates of application of the N-aryl-amidrazone compounds may be used dependent upon the prevailing environmental circumstances such as population density, degree of infestation, stage of plant growth, soil conditions, weather conditions and the like.

Advantageously, the compounds of the invention may be used in conjunction with, or in combination with other biological and chemical control agents including other insecticides, nematicides, acaricides, molluscicides, fungicides and bactericides such as nuclear polyhedrosis viruses, pyrroles, arylpyrroles, halobenzoylureas, pyrethroids, carbemates, phosphates, and the like.

Typical formulations suitable for the formula I compounds of the invention are granular compositions, flowable compositions, wettable powders, dusts, micro-emulsions, emulsifiable concentrates and the like. All compositions which lend themselves to soil, water and foliage application and provide effective plant protection are suitable. Compositions of the invention include the formula I N-arylamidrazone amide compound admixed with an inert solid or liquid carrier.

Where compositions of the invention are to be employed in combination treatments with other biological or chemical agents, the composition may be applied as an admixture of the components or may be applied sequentially.

For a more clear understanding of the invention, specific examples thereof are set forth below. These examples are merely illustrative, and are not to be understood as limiting the scope and underlying principles of the invention in any way.

EXAMPLE 1

Preparation of 2,2-Dimethylpropionic acid,2-(2,6- dichloro-α,α,α-trifluoro-p-tolyl)hydrazide ##STR10##

A solution of 2,6-dichloro-4-(trifluoro-methyl)phenylhydrazine (50.0 g, 0.20 mol) in methylene chloride is treated dropwise with trimethylacetyl chloride (30.6 g, 0.254 mol), stirred for 30 minutes, treated with 10% aqueous NaOH and stirred for 3 hours. The phases are separated; the organic phase is washed with water, dried over MgSO₄ and concentrated in vacuo to give an off-white solid residue. The solid is recrystallized from 1,2-dichloroethane to give the title product as a white solid, 55 g (82% yield), mp 140°-141°, identified by ¹ HNMR, ¹³ CNMR and IR spectral analyses.

EXAMPLES 2-42

Preparation of substituted N-arylhydrazide derivatives ##STR11##

Using essentially the same procedure described above for Example 1 and substituting the appropriate aryl-hydrazine and acid chloride, the compounds shown in

                                      TABLE I                                      __________________________________________________________________________      ##STR12##                                                                     Example                                                                        Number                                                                              A    B    W    Yn  R                mp °C.                         __________________________________________________________________________      2   CCl  CH   CCF.sub.3                                                                           6-Cl                                                                               (CH.sub.3).sub.2 CHCH.sub.2                                                                     135-136                                3   CCl  CH   CCl  6-Cl                                                                               (CH.sub.3).sub.3 C                                                                              124-125.5                              4   CCl  CH   CH   6-Cl                                                                               (CH.sub.3).sub.3 C                                                                              114-115                                5   CBr  CH   CCF.sub.3                                                                           6-Br                                                                               (CH.sub.3).sub.3 C                                                                              118-120                                6   CBr  CH   CCF.sub.3                                                                           6-Br                                                                               CH.sub.3         173-175                                7   CBr  CH   CCF.sub.3                                                                           6-Br                                                                               C.sub.6 H.sub.5  181-184                                8   CCH.sub.3                                                                           CH   CCl  H   (CH.sub.3).sub.3 C                                                                              103-106                                9   CCl  CH   CCF.sub.3                                                                           6-Cl                                                                               (CH.sub.3).sub.3 CCH.sub.2                                                                      125-127                               10   CCl  CH   CCl  6-Cl                                                                               pClC.sub.6 H.sub.5                                                                              188-190                               11   CCl  CH   CCF.sub.3                                                                           6-Cl                                                                               (CH.sub.3).sub.2 CH                                                                             158-159                               12   CCl  CH   CCl  6-Cl                                                                               cylopropyl       186-188                               13   CCl  CH   CCF.sub.3                                                                           6-Cl                                                                               CH.sub.3 CH.sub.2 C(CH.sub.3).sub.2                                                             121-123                               14   CH   CH   CCF.sub.3                                                                           H   (CH.sub.3).sub.3 C                                                                              136-139                               15   CCl  CH   CCF.sub.3                                                                           H   (CH.sub.3).sub.3 C                                                                              143-145                               16   CCl  CH   CCF.sub.3                                                                           6-Cl                                                                                ##STR13##       125-127                               17   CCl  CCl  CCl  5,6-diCl                                                                           (CH.sub.3).sub.3 C                                     18   N    CH   CCF.sub.3                                                                           6-Cl                                                                               (CH.sub.3).sub.3 C                                                                              151-151.5                             19   CCl  CH   CCl  6-Cl                                                                                ##STR14##       138-140                               20   CCl  CH   CCF.sub.3                                                                           6-Cl                                                                               pClC.sub.6 H.sub.5 OC(CH.sub.3).sub.2                                                           137-139                               21   CCF.sub.3                                                                           CH   CH   H   (CH.sub.3).sub.3 C                                                                               98-100                               22   CCl  CH   CCF.sub.3                                                                           6-Cl                                                                                ##STR15##       101-103                               23   CCl  CH   CCl  6-Cl                                                                               cyclohexyl       188-189                               24   CCl  CH   CCF.sub.3                                                                           6-Cl                                                                               C.sub.6 H.sub.5 C(CH.sub.3).sub.2                                                               104-105                               25   CCl  CH   CCl  6-Cl                                                                               CF.sub.3 CF.sub.2                                                                               131-132                               26   CCl  CH   CCl  6-Cl                                                                               (CH.sub.3).sub.2 CH                                                                             164-165                               27   CCl  CH   CCF.sub.3                                                                           6-Cl                                                                               cyclopropyl      172-174                               28   CCl  CH   CCl  6-Cl                                                                               CH.sub.3 CH.sub.2 C(CH.sub.3).sub.2                                                             132-134                               29   CCl  CH   CCF.sub.3                                                                           6-Cl                                                                                ##STR16##       160-162                               30   CBr  CH   CCF.sub.3                                                                           6-Br                                                                               (CH.sub.3).sub.3 C                                                                              140-141                               31   CCl  CH   CCl  6-Cl                                                                               CH.sub.3 (CH.sub.2).sub.5 C(CH.sub.3).sub.2            32   N    N    CCl  H   (CH.sub.3).sub.3 C                                                                              178-182                               33   CCl  CH   CCF.sub.3                                                                           6-Cl                                                                                ##STR17##       121-123                               34   CCl  CH   CCF.sub.3                                                                           6-Cl                                                                               pClC.sub.6 H.sub.5 C(CH.sub.3).sub.2                                                            105-107                               35   CCl  CH   CCF.sub.3                                                                           6-Cl                                                                               ClCH.sub.2 C(CH.sub.3).sub.2                                                                    119-120                               36   CCl  CH   CCF.sub.3                                                                           6-Cl                                                                                ##STR18##       174-175                               37   CCl  CH   CCl  6-Cl                                                                               ClCH.sub.2 C(CH.sub.3).sub.2                                                                    124-125                               38   CCl  CH   CH   5-CF.sub.3                                                                         (CH.sub.3).sub.3 C                                                                              170-177.5                             39   CCl  CH   CCF.sub.3                                                                           6-Cl                                                                               1-methylcyclohexyl                                                                              105-107                               40   CH   CCF.sub.3                                                                           CH   H   (CH.sub.3).sub.3 C                                                                              158-160                               41   CF   CF   CF   5,6-diF                                                                            (CH.sub.3).sub.3 C                                                                              154-157                               42   CBr  CH   F    6-Br                                                                               (CH.sub.3).sub.3 C                                                                              118-120                               __________________________________________________________________________

EXAMPLE 43

Preparation of 1-chloro-2,2-dimethylpropionaldehyde, 2-(2, 6-Dichloro-α,α,α-trifluoro-p-tolyl)hydrazone ##STR19##

A mixture of 2,2-dimethyl-2-(2,6-dichloro-α,α,α-trifluoro-p-tolyl)hydrazide propionic acid (50.0 g 0.152 mol) and thionyl chloride (53.8 g, 0,452 mol) in toluene is heated at reflux temperature for 8 hours, cooled to room temperature and concentrated in vacuo to give an oil residue. The oil is dissolved in hexanes and passed through a silica gel filtercake. The filter-cake is washed with several portions of hexanes. The filtrates are combined and concentrated in vacuo to give the title product as a yellow oil, 47.2 g (90% yield), identified by ¹ HNMR, ¹³ CNMR and IR spectral analyses.

EXAMPLES 44-84

Preparation of substituted N-arylhydrazinoyl chlorides ##STR20##

Using essentially the same procedure as described above in Example 43 and substituting the appropriate hydrazide substrate, the compounds shown in Table II are prepared and identified by ¹ HMR, ¹³ CNMR and IR spectral analyses.

                                      TABLE II                                     __________________________________________________________________________      ##STR21##                                                                     Example                                                                        Number                                                                              A    B    W    Yn  R                mp °C.                         __________________________________________________________________________     44   CCl  CH   CCF  6-Cl                                                                               (CH.sub.3).sub.2 CHCH.sub.2                            45   CCl  CH   CCl  6-Cl                                                                               (CH.sub.3).sub.3 C                                                                              44.5-45.5                             46   CCl  CH   CH   6-Cl                                                                               (CH.sub.3).sub.3 C                                     47   CBr  CH   CF   6-Br                                                                               (CH.sub.3).sub.3 C                                     48   CBr  CH   CCF.sub.3                                                                           6-Br                                                                               CH.sub.3                                               49   CBr  CH   CCF.sub.3                                                                           6-Br                                                                               C.sub.6 H.sub.5                                        50   CCH.sub.3                                                                           CH   CCl  H   (CH.sub.3).sub.3 C                                     51   CCl  CH   CCF.sub.3                                                                           6-Cl                                                                               (CH.sub.3).sub.3 CCH.sub.2                             52   CCl  CH   CCl  6-Cl                                                                               pClC.sub.6 H.sub.5                                                                              120                                   53   CCl  CH   CCF.sub.3                                                                           6-Cl                                                                               (CH.sub.3).sub.2 CH                                    54   CCl  CH   CCl  6-Cl                                                                               cyclopropyl                                            55   CCl  CH   CCF.sub.3                                                                           6-Cl                                                                               CH.sub.3 CH.sub.2 C(CH.sub.3).sub.2                    56   CH   CH   CCF.sub.3                                                                           H   (CH.sub.3).sub.3 C                                     57   CCl  CH   CCF.sub.3                                                                           H   (CH.sub.3).sub.3 C                                     58   CCl  CH   CCF.sub.3                                                                           6-Cl                                                                                ##STR22##                                             59   CCl  CCl  CCl  5,6-diCl                                                                           (CH.sub.3).sub.3 C                                     60   N    CH   CCF.sub.3                                                                           6-Cl                                                                               (CH.sub.3).sub.3 C                                     61   CCl  CH   CCl  6-Cl                                                                                ##STR23##                                             62   CCl  CH   CCF.sub.3                                                                           6-Cl                                                                               pClC.sub.6 H.sub.5 OC(CH.sub.3).sub.2                  63   CCF.sub.3                                                                           CH   CH   H   (CH.sub.3).sub.3 C                                     64   CCl  CH   CCF.sub.3                                                                           6-Cl                                                                                ##STR24##                                             65   CCl  CCH  CCl  6-Cl                                                                               cyclohexyl                                             66   CCl  CCH  CCF.sub.3                                                                           6-Cl                                                                               C.sub.6 H.sub.5 C(CH.sub.3).sub.2                      67   CCl  CH   CCl  6-Cl                                                                               CF.sub.3 CF.sub.2                                      68   CCl  CH   CCl  6-Cl                                                                               (CH.sub.3).sub.2 CH                                    69   CCl  CH   CCF.sub.3                                                                           6-Cl                                                                               cyclopropyl                                            70   CCl  CH   CCl  6-Cl                                                                               CH.sub.3 CH.sub.2 C(CH.sub.3).sub.2                    71   CCl  CH   CCF.sub.3                                                                           6-Cl                                                                                ##STR25##       110-111                               72   CBr  CH   CCF.sub.3                                                                           6-Br                                                                               (CH.sub.3).sub.3 C                                     73   CCl  CH   CCl  6-Cl                                                                               CH.sub.3 (CH.sub.2).sub.5 C(CH.sub.3).sub.2            74   N    N    CCl  H   (CH.sub.3).sub.3 C                                     75   CCl  CH   CCF.sub.3                                                                           6-Cl                                                                                ##STR26##                                             76   CCl  CH   CCF.sub.3                                                                           6-Cl                                                                               pClC.sub.6 H.sub.5 C(CH.sub.3).sub.2                                                             85-88                                77   CCl  CH   CCF.sub.3                                                                           6-Cl                                                                               ClCH.sub.2 C(CH.sub.3).sub.2                           78   CCl  CH   CCF.sub.3                                                                           6-Cl                                                                                ##STR27##        71-73                                79   CCl  CH   CCl  6-Cl                                                                               ClCH.sub.2 C(CH.sub.3).sub.2                           80   CCl  CH   CH   5-CF.sub.3                                                                         (CH.sub.3).sub.3 C                                     81   CCl  CH   CCF.sub.3                                                                           6-Cl                                                                               1-methylcyclohexyl                                     82   CH   CCF.sub.3                                                                           CH   H   (CH.sub.3).sub.3 C                                     83   CH   CH   CH   5-F (CH.sub.3).sub.3 C                                     84   CBr  CH   F    6-Br                                                                               (CH.sub.3).sub.3 C                                     __________________________________________________________________________

EXAMPLE 85

Preparation of N-Ethyl-2,2-dimethylpropionamide, 2-(2,6- Dichloro-α,α,α-trifluoro-p-tolylhydrazone ##STR28##

A solution of (2,6-dichloro-α,α,α-trifluoro-p-tolyl)hydrazone 1-chloro-2,2-dimethylpropionaldehyde (20.0 g, 0.0575 mol) in tetrahydrofuran is treated dropwise with 70% aqueous ethylamine (28.0 g, 0.144 mol) at room temperature, stirred for 1 hour and concentrated in vacuo to give a semi-solid residue. The semi-solid is dispersed in ether and water. The phases are separated; the organic phase is washed with water, dried over MgSO₄ and concentrated in vacuo to give the title product as a yellow oil, 19.8 g (97% yield), identified by ¹ HNMR, ¹³ CNMR and IR spectral analyses.

EXAMPLES 86-169

Preparation of substituted N-arylamidrazones ##STR29##

Using essentially the same procedure described above in Example 85 and substituting the appropriate hydrazinoylchloride and a suitable amine, the compounds shown in Table III are prepared and identified by ¹ HNMR, ¹³ CNMR and IR spectral analyses.

Hydrochloride salts of the invention may be prepared in accordance with the procedure outlined below.

EXAMPLE 146

Preparation of N-Ethyl-2,2-dimethyl-proprionamide, 2-(2,6-dichloro-α,α,α-trifluoro-p-tolylhydrazone hydrochloride ##STR30##

A stirred mixture of N-ethyl-2,2-dimethylpropionamide, 2-(2,6-dichloro-α,α,α-trifluoro-p-tolylhydrazone (0.1 g, 2.8 mmol) and hexane is bubbled through with HCl gas for a 30 minute period. The resultant reaction mixture is filtered to give the title compound as a white solid, 1.13 g, mp 202°-202.5°0 C.

                                      TABLE III                                    __________________________________________________________________________      ##STR31##                                                                     Example                                                                        Number                                                                              A    B   W    Yn  R        R2          R3   mp °C.                 __________________________________________________________________________      86  CCl  CH  CCF.sub.3                                                                           6-Cl                                                                               (CH.sub.3).sub.3 C                                                                      pClC.sub.6 H.sub.5                                                                         H                                   87  CCl  CH  CCl  6-Cl                                                                               (CH.sub.3).sub.3                                                                        CH.sub.3 CH.sub.2 CH.sub.2                                                                 H                                   88  CCl  CH  CCl  6-Cl                                                                               (CH.sub.3).sub.2 CH                                                                     CH.sub.3 CH.sub.2 CH.sub.2                                                                 H      48-50                        89  CCl  CH  CCF.sub.3                                                                           6-Cl                                                                               (CH.sub.3).sub.3 CCH.sub.2                                                              CH.sub.3 CH.sub.2 CH.sub.2                                                                 H                                   90  CCl  CH  CCl  6-Cl                                                                               (CH.sub.3).sub.2 CH                                                                     cyclopropyl H                                   91  CCl  CH  CCF.sub.3                                                                           6-Cl                                                                               (CH.sub.3).sub.3 CCH.sub.2                                                              CH.sub.3 CH.sub.2                                                                          H                                   92  CCl  CH  CCF.sub.3                                                                           6-Cl                                                                               (CH.sub.3).sub.2 CH                                                                     CH.sub.3 CH.sub.2                                                                          H      62-64                        93  CCl  CH  CCF.sub.3                                                                           6-Cl                                                                               (CH.sub.3).sub.3 C                                                                      CF.sub.3 CH.sub.3                                                                          H                                   94  CBr  CH  CCF.sub.3                                                                           6-Br                                                                               (CH.sub.3).sub.3 C                                                                      CH.sub.3 CH.sub.2                                                                          H                                   95  CBr  CH  CCF.sub.3                                                                           6-Br                                                                               (CH.sub.3).sub.3 C                                                                      CH.sub.3 CH.sub.2 CH.sub.2                                                                 H                                   96  CBr  CH  CCF.sub.3                                                                           6-Br                                                                               (CH.sub.3).sub.3 C                                                                      C.sub.6 H.sub.5 CH.sub.2                                                                   H                                   97  CBr  CH  CCF.sub.3                                                                           6-Br                                                                               (CH.sub.3).sub.3 C                                                                      furfuryl    H                                   98  CBr  CH  CCF.sub.3                                                                           6-Br                                                                               CH.sub.3 CH.sub.3 CH.sub.2                                                                          H                                   99  CBr  CH  CCF.sub.3                                                                           6-Br                                                                               C.sub.6 H.sub.5                                                                         CH.sub.3 CH.sub.2                                                                          H                                  100  CCl  CH  CCl  6-Cl                                                                               (CH.sub.3).sub.3 C                                                                      H           H     131-135                      101  CCl  CH  CCl  6-Cl                                                                               (CH.sub.3).sub.3 C                                                                      CH.sub.3    CH.sub.3                                                                              61-63                       102  CCl  CH  CCl  6-Cl                                                                               (CH.sub.3).sub.3 C                                                                      CH.sub.3 CH.sub.2                                                                          H                                  103  CCl  CH  CCF.sub.3                                                                           H   (CH.sub.3).sub.3 C                                                                      CH.sub.3 CH.sub.2 CH.sub.2                                                                 H                                  104  CCl  CH  CH   6-Cl                                                                               (CH.sub.3).sub.3 C                                                                      CH.sub.3 CH.sub.2 CH.sub.2                                                                 H                                  105  CCl  CH  CCF.sub.3                                                                           6-Cl                                                                               (CH.sub.3).sub.3 C                                                                      H           H     100-102.5                    106  CCl  CH  CCF.sub.3                                                                           6-Cl                                                                               (CH.sub.3).sub.3 C                                                                      CH.sub.3    H      78-79.5                     107  CCl  CH  CCF.sub.3                                                                           6-Cl                                                                               (CH.sub.3).sub.3 C                                                                      CH.sub.3    CH.sub.3                           108  CCl  CH  CCF.sub.3                                                                           6-Cl                                                                               (CH.sub.3).sub.3 C                                                                      CH.sub.3 CH.sub.2 CH.sub.2                                                                 H                                  109  CCl  CH  CCF.sub.3                                                                           6-Cl                                                                               (CH.sub.3).sub.3 C                                                                      (CH.sub.3).sub.3 C                                                                         H    67.5-68.5                     110  CCl  CH  CCF.sub.3                                                                           6-Cl                                                                               (CH.sub.3).sub.3 C                                                                      (CH.sub.3).sub.2 CHCH.sub.2                    111  CCl  CH  CCF.sub.3                                                                           6-Cl                                                                               (CH.sub.3).sub.3 C                                                                      CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2            112  CCl  CH  CCl  6-Cl                                                                               cyclopropyl                                                                             CH.sub.3 CH.sub.2                                                                          H      65-67                       113  CCl  CH  CCF.sub.3                                                                           6-Cl                                                                               CH.sub.3 CH.sub.2 C(CH.sub.3).sub.2                                                     CH.sub.3 CH.sub.2                                                                          H                                  114  CBr  CH  CCF.sub.3                                                                           6-Br                                                                               (CH.sub.3).sub.3 C                                                                      (CH.sub.3).sub.2 CH                                                                        H                                  115  CCl  CH  CCF.sub.3                                                                           H   (CH.sub.3).sub.3 C                                                                      CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2            116  CCl  CH  CCF.sub.3                                                                           6-Cl                                                                               CH.sub.3 CH.sub.2 C(CH.sub.3).sub.2                                                     CH.sub.3 CH.sub.2                                                                          CH.sub.3 CH.sub.2                  117  CCl  CH  CCF.sub.3                                                                           H   (CH.sub.3).sub.3 C                                                                      CH.sub.3 CH.sub.2                                                                          H                                  118  CCl  CH  CCl  6-Cl                                                                               CH.sub.3 CH.sub.2 C(CH.sub.3).sub.2                                                     CH.sub.3 CH.sub.2                                                                          H                                  119  CCl  CH  CCF.sub.3                                                                           6-Cl                                                                               C.sub.6 H.sub.5 C(CH.sub.3).sub.2                                                       CH.sub.3 CH.sub.2                                                                          H                                  120  CCl  CH  CCF.sub.3                                                                           H   (CH.sub.3).sub.3 C                                                                      CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                                            CH.sub.2                                       121  CH   CH  CCF.sub.3                                                                           H   (CH.sub.3).sub.3 C                                                                      CH.sub.3 CH.sub.2                                                                          H                                  122  CH   CH  CCF.sub.3                                                                           6-Cl                                                                               (CH.sub.3).sub.2 CHCH.sub.2                                                             CH.sub.3 CH.sub.2                                                                          H    86.5-88.5                     123  CCl  CH  CCF.sub.3                                                                           6-Cl                                                                               (CH.sub.3).sub.3 C                                                                      CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                                            CH.sub.2                                       124  CCl  CH  CCF.sub.3                                                                           6-Cl                                                                               (CH.sub.3).sub.3 C                                                                      cyclohexyl  H                                  125  CCl  CH  CCF.sub.3                                                                           6-Cl                                                                               (CH.sub.3).sub.3 C                                                                      C.sub.6 H.sub.5 CH.sub.2 CH.sub.2                                                          H                                  126  CBr  CH  CF   6-Br                                                                               (CH.sub.3).sub.3 C                                                                      CH.sub.3 CH.sub.2                                                                          H                                  127  CCl  CCl CCl  5,6-diCl                                                                           (CH.sub.3).sub.3 C                                                                      CH.sub.3 CH.sub.2                                                                          H      63-65                       128  CCl  CH  CCl  6-Cl                                                                               CH.sub.3 (CH.sub.2).sub.5 C(CH.sub.3).sub.2                                             CH.sub.3 CH.sub.2                                                                          H                                  129  CCl  CH  CCF.sub.3                                                                           6-Cl                                                                                ##STR32##                                                                              CH.sub.3 CH.sub.2                                                                          H                                  130  CCl  CH  CCF.sub.3                                                                           6-Cl                                                                               (CH.sub.3).sub.3 C                                                                      CH.sub.3 (CH.sub.2).sub.2 CH.sub.2                                                         H                                  131  CCl  CH  CCF.sub.3                                                                           6-Cl                                                                               (CH.sub.3).sub.3 C                                                                      (CH.sub.3).sub.2                                                                           H                                  132  CCl  CH  CCF.sub.3                                                                           6-Cl                                                                               (CH.sub.3).sub.3 C                                                                       ##STR33##  H                                  133  CCl  CH  CCl  6-Cl                                                                               pClC.sub.6 H.sub.5                                                                      (CH.sub.3).sub.2 CH                                                                        H     124-127                      134  CCl  CH  CCl  6-Cl                                                                               pClC.sub.6 H.sub.5                                                                      CH.sub.3 CH.sub.2                                                                          H     127-132                      135  CCl  CH  CCF.sub.3                                                                           6-Cl                                                                               C.sub.6 H.sub.5 C(CH.sub.3).sub.2                                                       C.sub.6 H.sub.5 CH.sub.2 CH.sub.2                                                          H                                  136  CCl  CH  CCF.sub.3                                                                           6-Cl                                                                                ##STR34##                                                                              CH.sub.3 CH.sub.2                                                                          H      74-75                       137  CCF.sub.3                                                                           CH  CH   H   (CH.sub.3).sub.3 C                                                                      CH.sub.3 CH.sub.2                                                                          H                                  138  CCl  CH  CCF.sub.3                                                                           H   (CH.sub.3).sub.3 C                                                                      C.sub.6 H.sub.5 CH.sub.2 CH.sub.2                                                          H                                  139  CCl  CH  CCF.sub.3                                                                           H   (CH.sub.3).sub.3 C                                                                       ##STR35##  H                                  140  CH   CH  CCF.sub.3                                                                           H   (CH.sub.3).sub.3 C                                                                       ##STR36##  H                                  141  CCl  CH  CCF.sub.3                                                                           6-Cl                                                                               pClC.sub.6 H.sub.5 C(CH.sub.3).sub.2                                                    CH.sub.3 CH.sub.2                                                                          H                                  142  CCl  CH  CCF.sub.3                                                                           6-Cl                                                                               (CH.sub.3).sub.3 C                                                                      C.sub.6 H.sub.5 CH(CH.sub.3)                                                               H                                  143  CCl  CH  CCF.sub.3                                                                           6-Cl                                                                               (CH.sub.3).sub.3 C                                                                      (CH.sub.3).sub.2 NCH.sub.2 CH.sub.2                                                        H                                  144  CCl  CH  CCF.sub.3                                                                           6-Cl                                                                               (CH.sub.3).sub.3 C                                                                      CH.sub.3 CH.sub.2 C(CH.sub.3).sub.2                                                        H                                  145  CCl  CH  CCF.sub.3                                                                           6-Cl                                                                               (CH.sub.3).sub.3 C                                                                       ##STR37##  H    100.5-101.5                    146*                                                                               CCl  CH  CCF.sub.3                                                                           6-Cl                                                                               (CH.sub.3).sub.3 C                                                                      CH.sub.3 CH.sub.2                                                                          H     202-202.5                    147  CBr  CH  CCF.sub.3                                                                           6-Br                                                                               (CH.sub.3).sub.3 C                                                                       ##STR38##  H                                  148  CCl  CH  CCF.sub.3                                                                           6-Cl                                                                                ##STR39##                                                                              CH.sub.3 CH.sub.2                                                                          H                                  149  CCl  CH  CCF.sub.3                                                                           6-Cl                                                                                ##STR40##                                                                              CH.sub.3 CH.sub.2                                                                          H                                  150  CCl  CH  CCF.sub.3                                                                           6-Cl                                                                               CH.sub.3 CH.sub.2 C(CH.sub.3).sub.2                                                     C.sub.6 H.sub.5 CH.sub.2 CH.sub.2                                                          H                                  151  CCl  CH  CCF.sub.3                                                                           6-Cl                                                                               (CH.sub.3).sub.3 C                                                                      C.sub.6 H.sub.5 CH.sub.2                                                                   H                                  152  CCl  CH  CCF.sub.3                                                                           6-Cl                                                                               (CH.sub.3).sub.3 C                                                                      CH.sub.3 CH.sub.2                                                                          CH.sub.3 CH.sub.2                  153  CCl  CH  CCF.sub.3                                                                           6-Cl                                                                                ##STR41##                                                                              CH.sub.3 CH.sub.2                                                                          H                                  154  CCl  CH  CCF.sub.3                                                                           6-Cl                                                                                ##STR42##                                                                              (CH.sub.3).sub.2 CH                                                                        H                                  155  CCl  CH  CCF.sub.3                                                                           6-Cl                                                                               ClCH.sub.2 C(CH.sub.3).sub.2                                                            pCF.sub.3 OC.sub.6 H.sub.5                                                                 H     203-205                      156  CCl  CH  CCF.sub.3                                                                           6-Cl                                                                               (CH.sub.3).sub.3 C                                                                      neopentyl   H                                  157  CCl  CH  CCF.sub.3                                                                           6-Cl                                                                               (CH.sub.3).sub.3 C                                                                      H.sub.2 NCOCCH(CH.sub.3).sub.2                                                             H     160-162                      158  CCl  CH  CCF.sub.3                                                                           6-Cl                                                                               (CH.sub.3).sub.3 C                                                                       ##STR43##                                     159  CCl  CH  CCF.sub.3                                                                           6-Cl                                                                               (CH.sub.3).sub.3 C                                                                      pClC.sub.6 H.sub.5 CH.sub.2 CH.sub.2                                                       H                                  160  CCl  CH  CCF.sub.3                                                                           6-Cl                                                                               (CH.sub.3).sub.3 C                                                                       ##STR44##  H                                  161  CCl  CH  CCF.sub.3                                                                           6-Cl                                                                               (CH.sub.3).sub.3 C                                                                       ##STR45##  H                                  162  CCl  CH  CCF.sub.3                                                                           6-Cl                                                                               (CH.sub.3).sub.3 C                                                                      CH.sub.3 (CH.sub.2).sub.4 CH(CH.sub.3)                                                     H                                  163  CCl  CH  CCF.sub.3                                                                           6-Cl                                                                               (CH.sub.3).sub.3 C                                                                      (C.sub.2 H.sub.5).sub.2 N(CH.sub.2).sub.3                                      CH(CH.sub.3)                                                                               H                                  164  CCl  CH  CCF.sub.3                                                                           6-Cl                                                                               (CH.sub.3).sub.3 C                                                                      CH.sub.2 CHCH.sub.2                                                                        H                                  165  CCl  CH  CCF  6-Cl                                                                               1-methylcyclohexyl                                                                      CH.sub.3 CH.sub.2                                                                          H                                  166  CCl  CH  CH   5-CF.sub.3                                                                         (CH.sub.3).sub.3 C                                                                      CH.sub.3 CH.sub.2                                                                          H                                  167  CF   CF  CF   5,6-diF                                                                            (CH.sub.3).sub.3 C                                                                      CH.sub.3 CH.sub.2                                                                          H                                  168  CBr  CH  CF   6-Br                                                                               (CH.sub.3).sub.3 C                                                                      CH.sub.3 CH.sub.2                                                                          H                                  169  CCl  CH  CCF.sub.3                                                                           6-Cl                                                                               (CH.sub.3).sub.3 C                                                                       ##STR46##  H                                  __________________________________________________________________________      *Hydrochloride salt                                                      

EXAMPLE 170

Insecticidal and Acaricidal Evaluation of N-aryl-amidrazone compounds

Test solutions are prepared by dissolving the test compound in a 35% acetone in water mixture to give a concentration of 10,000 ppm. Subsequent dilutions are made with water as needed.

Spodoptera eridania, 3rd instar larvae, southern armyworm

A Sieva limabean leaf expanded to 7-8 cm in length is dipped in the test solution with agitation for 3 seconds and allowed to dry in a hood. The leaf is then placed in a 100×10 mm petri dish containing a damp filterpaper on the bottom and ten 3rd instar caterpillars. At 3 and 5 days, observations are made of mortality, reduced feeding, or any interference with normal molting.

Tetranychus urticae(OP-resistant strain), 2-spotted spider mite

Sieva limabean plants with primary leaves expanded to 7-8 cm are selected and cut back to one plant per pot. A small piece is cut from an infested leaf taken from the main colony and placed on each leaf of the test plants. This is done about 2 hours before treatment to allow the mites to move over to the test plant to lay eggs. The size of the cut, infested leaf is varied to obtain about 100 mites per leaf. At the time of test treatment, the piece of leaf used to transfer the mites is removed and discarded. The newly mite-infested plants are dipped An the test solution for 3 seconds with agitation and set in the hood to dry. After 2 days, one leaf is removed and mortality counts are made. After 5 days, another leaf As removed and observations are made of mortality of the eggs and/or newly emerged nymphs.

Diabrotic undecimpunctata howardi, 3rd instar southern corn rootworm

One cc of fine talc is placed in a 30 ml wide-mouth screw-top glass jar. One mL of the appropriate acetone test solution is pipetted onto the talc so as to provide 1.25 mg of active ingredient per jar. The jars are set under a gentle air flow until the acetone is evaporated. The dried talc is loosened, 1 cc of millet seed is added to serve as food for the insects and 25 mL of moist soil is added to each jar. The jar is capped and the contents thoroughly mixed on a Vortex Mixer. Following this, ten 3rd instar rootworms are added to each jar and the jars are loosely capped to allow air exchange for the larvae. The treatments are held for 6 days when mortality counts are made. Missing larvae are presumed dead, since they decompose rapidly and can not be found. The concentrations used in this test correspond approximately to 50 kg/ha.

The data obtained are shown in Table IV.

                  TABLE IV                                                         ______________________________________                                         Insecticidal and Acaricidal Evaluation                                         of N-Arylamidrazones                                                           % Mortality                                                                    Compound                                                                               Armyworm.sup.1                                                                             2-Spotted Mite.sup.2                                                                       Corn Rootworm.sup.3                            (Ex. No.)                                                                              (300 ppm)   (300 ppm)   (50 kg/ha)                                     ______________________________________                                          85     0           0           100                                             86     100         0            80                                             87     40          90          100                                             88     --          --          --                                              89     0           0           100                                             90     0           0            20                                             91     0           80          100                                             92     0           0           100                                             93     0           0           100                                             94     --          80          100                                             95     80          0           100                                             96     100         40           80                                             97     0           0           100                                             98     40          0            40                                            100     0           40           0                                             101     0           0            60                                            102     0           60          100                                            103     40          0           100                                            104     0           90           50                                            105     20          0            90                                            106     40          0           100                                            107     --          --          100                                            108     90          50          100                                            109     0           0            50                                            110     0           0           100                                            111     100         40           90                                            112     40          100          20                                            113     20          100         100                                            114     40          100         100                                            115     0           0           100                                            116     20          50          100                                            117     20          0           100                                            118     50          70          100                                            119     100         50           90                                            120     --          30           20                                            121     80          40          100                                            122     0           0            40                                            123     0           0            60                                            124     50          80          100                                            125     0           30          100                                            126     0           80           90                                            128     0           0            30                                            129     100         40           0                                             130     80          80          100                                            131     70          0           100                                            132     --          40          100                                            133     --          0            0                                             134     0           30           0                                             135     0           0            0                                             136     0           70          100                                            137     0           0           100                                            138     0           0           100                                            139     0           70          100                                            140     0           0            50                                            141     100         0            0                                             142     0           0           100                                            143     0           0           100                                            144     0           0           100                                            145     0           0           100                                            146     0           0           100                                            147     0           0           100                                            148     50          0           100                                            149     100         80           80                                            150     0           60          100                                            152     80          0           100                                            153     100         0           100                                            156     --          0           100                                            157     0           0           100                                            158     40          0           100                                            159     0           0           100                                            160     0           0           100                                            161     0           0           --                                             162     0           100         100                                            163     0           0           100                                            164     0           0           100                                            167     0           0           100                                            168     0           80           90                                            169     0           0           100                                            ______________________________________                                          .sup.1 Armyworm is 3rd instar larvae, southern armyworm                        .sup.2 2Spotted Mite is 2spotted spider mite (OPresistant)                     .sup.3 Corn Rootworm is 3rd instar southern corn rootworm                 

What is claimed is:
 1. A compound having the structure of formula I ##STR47## wherein A is C--R₄ ;B is C--R₅ ; W is C--R₆ ; Y is halogen, CN, C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, C₁ -C₆ alkoxy or C₁ -C₆ haloalkoxy; n is an integer of 0, 1 or 2; R is C₁ -C₁₀ alkyl optionally substituted with one or more halogens,C₃ -C₆ cycloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, (C₁ -C₄ alkyl)SO_(x), (C₁ -C₄ haloalkyl)SO_(x), phenyl optionally substituted with one to three halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, (C.sub. -C₄ alkyl)SO_(x), (C.sub. -C₄ haloalkyl)-SO_(x), NO₂ or CN groups, or phenoxy optionally substituted with one to three halogen, C₁ -C₄ alkyl, C.sub. -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, (C₁ -C₄ alkyl)SO_(x), (C₁ -C₄ haloalkyl)SO_(x), NO₂ or CN groups, C₃ -C₁₂ cycloalkyl optionally substituted with one or more halogens,C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, (C₁ -C₄ alkyl)SO_(x), (C₁ -C₄ haloalkyl)SO_(x), phenyl optionally substituted with one to three halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, NO₂ or CN groups, or phenoxy optionally substituted with one to three halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, NO₂ or CN groups; R₁ is hydrogen; R₂ and R₃ are each independently hydrogen,C₁ -C₁₀ alkyl optionally substituted with one or more halogen, hydroxy, C₁ -C₄ alkoxy,(C₁ -C₄ alkyl)SO_(x), CONR₇ R₈, CO₂ R₉ R₁₀, R₁₁, C₃ -C₆ cycloalkyl optionally substituted with one to three halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, NO₂ or CN groups, phenyl optionally substituted with one or more halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C.sub. -C₄ haloalkoxy, NO₂ or CN groups, or pyridyl optionally substituted with one or more halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, NO₂ or CN groups, C₃ -C₁₀ alkenyl optionally substituted with one or more halogen, hydroxy, C₁ -C₄ alkoxy, (C₁ -C₄ alkyl)SO_(x), CONR₇ R₈, CO₂ R₉, R₁₀, R₁₁,C₃ -C₆ cycloalkyl optionally substituted with one to three halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, NO₂ or CN groups, phenyl optionally substituted with one or more halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, NO₂ or CN groups, or pyridyl optionally substituted with one or more halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, NO₂ or CN groups, C₃ -C₁₀ alkynyl optionally substituted with one or more halogen, hydroxy, C₁ -C₄ alkoxy, (C₁ -C₄ alkyl)SO_(x), CONR₇ R₈, CO₂ R₉, R₁₀, R₁₁,C₃ -C₆ cycloalkyl optionally substituted with one to three halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, NO₂ or CN groups, phenyl optionally substituted with one or more halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, NO₂ or CN groups, or pyridyl optionally substituted with one or more halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, NO₂ or CN groups, C₃ -C₁₂ cycloalkyl optionally substituted with one or more halogen, hydroxy, C₁ -C₄ alkoxy, (C₁ -C₄ alkyl)SO_(x), CONR₇ R₈, CO₂ R₉, R₁₀, R₁₁,C₃ -C₆ cycloalkyl optionally substituted with one to three halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, NO₂ or CN groups, phenyl optionally substituted with one or more halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, NO₂ or CN groups, or pyridyl optionally substituted with one or more halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, NO₂ or CN groups or R₂ and R₃ may be taken together to form, a ring represented by the structure ##STR48## R₄, R₅ and R₆ are each independently hydrogen, halogen, CN, NO₂, (C₁ -C₄ alkyl)SO_(x), (C₁ -C₄ haloalkyl)SO_(x), C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, C₁ -C₆ alkoxy or C₁ -C₆ haloalkoxy; R₇, R₈ and R₉ are each independently hydrogen or C₁ -C₄ alkyl; R₁₀ is NR₁₂ R₁₃, ##STR49## R₁₁ is ##STR50## R₁₂, R₁₃, R₁₄ and R₁₅ are each independently hydrogen or C₁ -C₄ alkyl ; X is O, S or NR₁₄ ; r is an integer of 0 or 1; p and m are each independently an integer of 0, 1, 2 or 3 with the proviso that the sum of p+m+r must be 4, 5 or 6; x is an integer of 0, 1 or 2; or the acid addition salts thereof;with the proviso that one of R₂ and R₃ is other than hydrogen and with the further proviso that if R₄, R₅ and R₆ are all hydrogen then n cannot be
 0. 2. A compound having the structure ##STR51## wherein R is C₁ -C₁₀ alkyl;R₁ is hydrogen R₂ is C₁ -C₁₀ alkyl; R₃ is hydrogen or C₁ -C₁₀ alkyl; and R₄, R₆ and Y are each independently hydrogen, halogen, CN, C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, C₁ -C₆ alkoxy or C₁ -C₆ haloalkoxy.
 3. The compound according to claim 2 wherein R₁ are R₃ are hydrogen.
 4. The compound according to claim 3 wherein Y is halogen, R₄ and R₆ are each independently halogen or C₁ -C₆ alkyl substituted with one or more halogens.
 5. The compound according to claim 4 wherein Y is chlorine and R₆ is trifluoromethyl.
 6. The compound according to claim 4 wherein R is t-butyl and R₂ is ethyl.
 7. The compound according to claim 6 N-ethyl-2,2-dimethylpropionamide, 2-(2,6-dichloro-α,α,α trifluoro-p-tolylhydrazone. 